Colluded Individuals
by fadingtales
Summary: What do you have when you get Chuck Bass and Blair Waldorf lurking around in a dark alley way? Trouble.Takes place after 2x08, Chair, AU.
1. Chapter 1

**Title:** **Colluded Individuals****  
Author:** fading_tales  
**Pairing:** Chuck/Blair  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Summary****: **What do you have when you get Chuck Bass and Blair Waldorf lurking around in a dark alley way? Trouble.Takes place after 2x08, AU.

**A/N:** This little scene has been playing itself in my head for the longest time and finally I had the muse to inspire me to write it out. I don't know how long yet I'm planning this fic to be, probably not as long as SDB. Let me know what you guys think of it so far! Please read and review! 3

**Chapter One**

Blair Waldorf has been known to stick her nose in places where it doesn't belong. This inquisitive compulsion is what made her queen in the first place. So when Blair goes snooping for some dirt on a rival bitch, and instead finds New York's resident billionaire playboy Chuck Bass lurking in the shadows of some dark alley instead of the trendy hip clubs he is usually spotted in, her interest is definitely piqued.

For a moment she considers her options. She could go on her merry way and pretend to have not witness another Bass crime in the making _or_… follow the white rabbit into whatever hellish hole it leads and go join the Basstard in his devious venture. She didn't really have to think all that long before tip-toeing as quietly as she could physically manage in her sky high Manolos and sneaking up behind said Basstard.

Her efforts go unappreciated when she stumbles from a crack on the dirty broken concrete and Chuck notices her. He narrows his eyes as she drops all pretenses of being incognito and instead purposefully struts her way to his side.

"Who would have guessed that Chuck Bass would be living a double life? Sleazy cocky asshole by day, sleazy cocky asshole with a trench coat by night," She says it with a smug smirk that reaches her eyes.

"And who would have guessed that Blair Waldorf was a scheming, manipulative, self-serving bitch? Oh wait, that would be everyone."

"Takes one to know one," she says in a sing-song voice.

He watches her as she prances about the alley, scrunching her nose at a pile of cardboard boxes and other various trash items in one corner.

"What _is_ it that you're doing anyways? Is being a billionaire's son just too boring? I never would have pictured you'd have business in some dinky little alley in Midtown."

"The question should be what the hell are _you_ doing here, Waldorf?" He sighs. "Don't you have some petty UES rival bitch to destroy?"

"Precisely. I _was_ gathering intel on that Montgomery skank from the Spence varsity volleyball team, when who is it but the one and only Chuck Bass hiding in the shadows that attracted my attention."

"Are you sure it was my hiding in the shadows that _attracted_ your attention?" he asks smarmily.

She merely rolls her eyes at his comment; it's almost a conditioned response by now.

"Volleyball… I've always wondered why you never tried out. What with those lovely mile long legs of yours and those tight little shorts…" he emphasizes the words with a suggestive glance down towards her aforementioned lovely pair of legs. "There'd be a reason to actually go to gym class."

"You disgust me."

"And yet you're still here," Chuck says with a genuine Bass smile.

They were still playing at a mockery of a relationship. Pining glances and flirty remarks that only results in the both of them going home alone at the end of the day.

"So what did the short shorts wearing volleyball 'skank' do to you anyways?"

"The bitch thought she could wear the same dress as me at the Black and White fundraiser for pandas at the zoo."

"Seriously, Blair? There's got to be something more to it than that. You don't even like pandas."

"Pandas are _bears_! People think they're all cute and cuddly, but those things have claws and teeth!"

"Very much like someone I know."

"And what exactly would you know? You weren't even at that fundraiser. Probably too busy being a vigilante or whatever it is you're doing as of late."

She sounds a little accusatory with that line and so he answers with a cocked eyebrow.

"I assure you I'm not doing any masked-avenger-ing"

"Say what you will. I would have thought you'd be at least a bit cleverer with your disguise."

"I was going for hiding in plain sight."

"A difficult feat to accomplish when one is dressed like Inspector Gadget."

Despite the insults, they're both smiling.

"The next time I go snooping around dark alleys, I'll be sure to call you first and have you pick out my wardrobe."

"That's the first clever thing I've heard you say all day," she says with a satisfied smile.

"So, are you going to tell me what you're doing here anytime soon?"

He sighs, but gives in to her relentless prodding. "My father is trying to acquire a new building and that," he gestures to middle aged man standing across the street, "is the owner of said building who's waiting to meet up with his drug dealer."

"So…"

"So… I get some blackmail material that will convince the good fellow to expedite the deal-"

"And papa Bass will pat you on the head? Is this what you've been ditching a week's worth of class for?" Blair finishes.

He's face turns severe and she immediately regrets her words. Nevertheless, Blair had always harbored a sort of resentment towards the older Bass for his maltreatment of his son.

"This is why I didn't tell you anything."

"Look, Chuck. I get it that you want your father's approval, but you have to realize that sometimes it's just a lost cause."

"Says the girl with mommy issues."

Blair bites back the sting of his remark since she was the one that dealt the first blow.

"I just think you're wasting your time, trying to help him out and in the end he's going to just disappoint you."

"Well, I didn't ask for _your_ opinion, so why don't you go back to pathetically hanging on to that meaningless social throne of yours and leave me alone?"

Lines have been drawn and they've both crossed them. He doesn't look at her, but he can feel her stare boring holes in the back of his head. Stubborn fools they are. The sounds of her heels angrily clacking against the asphalt fades away and he begins his internal torment.


	2. Chapter 2

**Title:** **Colluded Individuals****  
Author:** fading_tales  
**Pairing:** Chuck/Blair  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Summary****: **What do you have when you get Chuck Bass and Blair Waldorf lurking around in a dark alley way? Trouble.Takes place after 2x08, AU.

**Chapter Two**

School is more torturous the next day than usual. He shows up during fifth period and she wonders why he even bothered. He sees her and attempts to approach, but she quickly out maneuvers him, taking refuge with Serena and allowing her minions to block his path. If anything, Blair Waldorf knows how to hold a grudge.

The school bell signaling the end of the day comes all too soon and her defenses quickly scatter to the four winds, suspicious all too busy and unresponsive to her demands.

"Helpless without your subjects, Blair?"

She should've known he wasn't going to let sleeping dogs lie. The memory of the harsh comments the day earlier bubble to the surface. She refuses to speak to him.

"Blair, come on. Stop being immature," he whines.

"I'm not the immature one here!" She retorts.

She's angry, as she should be, but he's grateful he has her at least speaking.

"Why don't we go get a drink? Go to Butter maybe."

"I don't feel like going to Butter."

"Then wherever you want. I'll have Arthur bring the car around."

She gives him a steady look that reads: no, no, and NO and swings her Chloe handbag over her shoulder.

"I'm busy, Chuck. Go back to whatever it is that you do nowadays. I won't be intruding on your dirty little secret anymore. My schedule's full and I'm already late for my appointment."

She doesn't spare him a glance as she marches off. He should've known it wasn't going to be easy.

---

She knows she is probably as much in the wrong as he was, maybe even more, but that doesn't mean she's not angry. Besides, if she gives him an inch now, who knows to what length he'll ask her to go to the next time around. The reason they worked, or didn't work, was because both of them shared a particular quality of stubbornness and pride.

She arrives at the Montgomery household, smirk in place, deadly envelope containing critical information regarding Sarah Montgomery in hand. She poses as the picture of Upper East Side elegance and is courteously let in. Mr. and Mrs. Montgomery gush over how wonderful it is she's come to pay their 'little Sarah' a visit. Blair knows Mr. Montgomery's firm is angling to land her mother as a client. Everyone knows that being new money and all, but not enough money as Bart Bass to be formidable, the Montgomery's are always trying to rub elbows with the old, traditional elite families of New York. So, Blair smiles a fake smile and says nice pleasant things while carefully biting back nasty comments that are itching to burst for her lips. There are proper times for certain things and soon the timing will be right to let his bitch flag fly.

"Thank you for you wonderful hospitality, Mr. and Mrs. Montgomery. I was just wondering if dear Sarah would be joining us soon?"

Patience is unfortunately not one of her many virtuous attributes.

"Oh yes! Let me go get her. The girl is probably up in her room studying as usual. You know how our Sarah gets about her studies. No distractions for her! It's all volleyball and school! She doesn't even have a boyfriend," Mrs. Montgomery rambles on as she mounts the stairs.

Blair restrains herself from commenting on what 'little Sarah' likes to do with boys after volleyball practice underneath bleachers. Instead Blair sips her tea and smiles politely at Mr. Montgomery.

A scream is heard from upstairs that startles both her and Sarah's dad. They both rush up the stairs to find out what's wrong. What they saw was the epitome of wrong. It was Chuck Bass fully clothed and lounging in a chair while Sarah Montgomery was topless and in her panties, haphazardly trying to cover up herself with a magazine. It soon becomes clear that Sarah was in the middle of a private strip show when her mother had caught her in the act. Hence the hysterics on the Montgomery matron's part.

Chuck watches as the chaos ensued. It was much more entertaining than the volleyball chick's awkward attempts at being seductive. _"Money just can't account for taste,"_ he laments mentally. Really, those satin, lacey, rhinestoned panties of hers just scream desperate and trying-too-hard in five different languages. He much rather enjoy the look of shock upon Blair's face, not for seeing Sarah being the slut that she is, but the fact that he was there and still clothed, stealing her vengeful thunder. His depravity knew no bounds.

"Well… thanks, Sarah for the offer on the um, _tutoring_ session. But I think I'm just going to borrow that history book that I asked for."

Chuck calmly makes his way past the Montgomery's, politely bidding good-bye to Sarah's parents. One could tell that Mr. Montgomery wanted very much to strangle Chuck, but seeing as his name is Bass and Montgomery & Associates main office is headquartered in one of Big Bart's many prime real estates, he bites his tongue and steady his hand. The anger and humiliation is instead projected on poor little Sarah, crying her eyes out and still clutching onto that magazine for dear life. Chuck drags a stunned Blair out the door while the family continued their little family "_talk_".

Once they're outside, Blair quickly recovers herself and quickly finds the scathing comments she couldn't think of before. Streams of colorful expletives and obscenities about Chuck come spilling out her mouth as he stands there taking it all in.

"What the hell are you _doing_ here?!" She screams at him.

"Clearing up your schedule," he replies with the same calmness as before. "Now that we've got the whole destroy the volleyball whore out of the way, you can come join me for that drink we talked about before."

He reaches for her arm to lead her to the waiting car, but she only slaps his hand away, adamantly rooted to her spot.

"You just totally ruined my plan! I spent precious time preparing to take down the bitch, victory within easy reach and _you_ just took it away from me!"

"What does it matter who destroys her? The point is that she's destroyed. I did it for you!"

"Oh! It must have been terrible for you to sit there and watch a girl strip for you. I'm just soooo grateful you suffered through that for me. Really! _Thank you_!" Blair mocks.

"You're _welcome_," he snaps.

She lets out a frustrated huff and proceeds to stomp away.

She thought it was so easy. As if he didn't have to grovel to Serena to find out where she was heading, slap together a plan to destroy the Sarah bitch that completely lacked the finesse he usually employed, basically winging the entire thing, all the while trying to beat her to the punch and being stealthy about it. If she thought the last hour had been anything simple or easy, she had another thing coming. And all of this for what? A fucking drink. That's all he asked of her. Never had Chuck Bass worked so hard to get a girl to go out and have a drink with him. Usually the rate he has girls flinging themselves at him is enough to require Arthur to double as a bodyguard. The nerve of her to rebuff his offer!

"You stop right there, Waldorf!"

"I will _not_!"

If he wasn't so angry, he'd be impressed by the rate she's going in those ten inch heels. He manages to catch up with her when she stumbles over a crack in the pavement. Blair mentally curses at gravity for always messing her up.

"Hey! Hey! Will you just look at me for a second?"

She crosses her arms defiantly and turns her head to face the opposite direction.

"You're making it awfully hard to say I'm sorry."

She still refuses to look at him.

"Did you hear that, Waldorf? I just said I'm sorry!"

"About?" she prods.

She never made things easy.

"About fucking everything. Everything is my fault, okay? Sorry, sorry, sorry! I'm apologizing for every fucking thing that has gone wrong now or will go wrong in the future in your perfect little life because of me."

He's hot, tired and embarrassed. This is the first time he's ever apologized to anyone. Ever needed to, ever cared to. And it's not even entirely his fault! She's the one that stumbled into his life and fucked everything he's ever known up and here he is apologizing to _her_. It's not as if she doesn't know she's a self-righteous, selfish bitch. He's not the only one with questionable morals here and yet he's the one in trouble for it. There are a lot of reasons for not apologizing. He said it anyways because it's better than not speaking to her, not seeing her, not being around her. She's silent and the humiliation grows exponentially.

All issues past become irrelevant with her next comment.

"I missed you."

It's three words, two letters too long. But it's close. She's irritating, infuriating, maddening. One minute she's angry with him, ready to claw out his eyes with her bare hands, and the next she's saying things that make him want to kiss her and never stop.

Blair Waldorf doesn't usually let her mask slip and he can't stop the hammering of his heart. The increase in his pulse rate doesn't change that fact that they had agreed to wait. Their pretenses as… whatever it is they are remains firmly in place. For all the rest of the world knows, Chuck and Blair are nothing out of the ordinary. Just a boy and a girl.

But then again, isn't that how every story starts?

"You haven't been in school lately. You don't come out with Nate or Serena or me anymore. I feel like ever since that night on the rooftop and our whole 'let's wait' thing, I don't even see you anymore. I know we can't be together, at least not yet. I know I said that there might even be some sort of excruciating pleasure in it, but all I feel is the excruciating and none of the pleasure."

At the moment, for the life of him he can't imagine why he'd want to wait.

"I'm sorry, too. About what I said yesterday... I didn't mean to –"

"Shut up, Waldorf."

And she promptly does. It's kind of hard to talk when his lips is pressing on hers.

His lips are slight rough and she darts out a tongue to moisten them. It becomes quickly entangled with his. Wasn't it Emmerson who asked, "How much of human life is lost in waiting?" Chuck decides he needs to start making up for lost time.

FIN?

**A/N:** This could end with this as a two part one shot, but I also have a bit of an idea of how to extend it although I don't have a clear ending in mind so updates will be sporadic. What do you guys think? A good ending? Continue?? Let me know! Reviews/comments = 3


	3. Chapter 3

**Title:** **Colluded Individuals****  
Author:** fading_tales  
**Pairing:** Chuck/Blair  
**Disclaimer:** I do not own Gossip Girl or any characters, they belong to the CW and Cecily von Ziegesar.  
**Rating:** PG-13 ~ T  
**Summary****: **What do you have when you get Chuck Bass and Blair Waldorf lurking around in a dark alley way? Trouble.Takes place after 2x08, AU.

**Chapter Three**

The next week is the Constance Billard versus Spence Academy volleyball game. Blair is satisfied to notice that a certain captain is absent. _Indefinitely,_ she heard. Poor little Sarah's parents has thought it might be in their daughter's best interest to be shipped to a Swiss boarding school for girls. After their first shocking discovery about their innocent little lamb's promiscuity, they also found an envelope in their mailbox containing scans of surveillance photos that incriminate Sarah with some drug dealing and using. Blair hadn't wanted some good intel work go to waste.

She watches the game as Constance owns the other team, smile permanently playing on her lips. A sense of superiority and all things right with the world blossoms in her chest.

"You seem to be enjoying the game."

She looks up to find Chuck Bass unprecedentedly present in gym class. He's not at all dressed for it by the looks of him and his Armani pants. But he's here. And that's all that matters.

"I hope this means you're considering my suggestion about you and a certain volleyball team uniform. Particularly the shorts. Maybe I could even help you put it on… or take it off…" his voice trails into that seductive low tone of his that makes her skin tingle and her nether regions grow hot.

"Sorry, Bass. I think I'm done with this whole volleyball business. As satisfying as destroying the Spence bitch as it was… I need an adversary that is actually up to my caliber."

"I'm glad you think so, too," a new voice calls out from behind them.

They both turn around to match the owner of the infamously villainous voice to none other than Georgina Sparks herself.

"Hi you guys. Did you miss me?" Georgina taunts with false camaraderie.

"If one can miss an ulcer," Blair bites out.

"Cancer might be a better word," Chuck chips in.

Georgina maintains her sunny façade amidst the snide remarks.

"I heard someone else became a casualty in one of your twisted games of foreplay. Swiss boarding school… I wonder if it's the same one I went to, if so I should recommend her to not miss out on morning mass, morning meals afterwards are surprisingly good. Particularly the organic oatmeal with blackberry and brown sugar."

"You must really like the sound of your own voice, the way you're going on rambling like this," Blair jibes.

"Shouldn't you be in boot camp?" Chuck drawls.

"Yes, go make use of those military training and march right on out the door."

"Oh, Blair. I'm on leave for good behavior."

"Good behavior… not something I would _ever_ think to associate with you," Blair replies with a mockingly skeptical look.

"Think whatever you want. The point is… I'm _back_. Consider this as the gauntlet being thrown down, Blair. Your days as the crazy bitch around here are soon ending. It's the dawn of a new reign. And this time you're not going to get rid of me so easily."

The devil herself puts on her sunglasses with a sneer.

"I'll see you guys around," she promises.

Georgina picks up her bag from its place on the bench and saunters away as Blair and Chuck watches.

Irksome as Whoregina may be, Chuck can't help but feel a bit excited about the possibility of someone worthy of their skill and savoir-faire in deceit and manipulation. Nothing gets Blair more worked up than a good take-down.

"So… who are we destroying this week?" he asks with an impish grin.

"Do you even need to ask?"

"Sparks won't know what hit her."

He has a mischievous glint in his eye that she recognizes. She's sure she has a matching devious twinkle in her own. Collusion has always been their forte.

As she goes on to list off malicious strategies and tactics they should partake against the she-devil, rivaling the expertise of a well seasons totalitarian military dictator, he can't help but realize how much he had missed her too.

"I adore you."

It's three words, one letter too long. They're getting closer to the right combination. If it were a game, he had strategically made it so that next time, when they get the combination right, it'll be her turn and she'll have to say those infamous three words, _eight_ letters first. But it's not a game and he's not sure if he can keep those words to himself any longer.

"Enough of the sweet talk, Bass. We have business to attend to," she chides, but not able to hide the rosy blush blossoming in her cheeks. He has the urge to place a kiss on the apples of those flushed cheeks.

"_I love you"_ lies on the tip of his tongue. He'll save it for when they wipe that cheeky smirk off of Sparks's insufferable face.

FIN?

**A/N: **This isn't exactly what I planned on if I was going to continue this story, but I was re-watching the Season One finale and so I got inspired. Everyone loves some Georgina Sparks don't they? Again… the fic could end with this chapter or continue… I just don't know which yet. _ This fic is sort of a spontaneous work in limbo for me in which sometimes my internal muse starts clicking away with ideas and other times my brain is fizzled.


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